A white neoclassical building with columns and a clock tower, surrounded by brick buildings and a clear blue sky.

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Check prices for these dates

Next weekend
Sep 25 - Sep 27
In two weeks
Oct 2 - Oct 4
In one month
Oct 16 - Oct 18
In two months
Nov 13 - Nov 15

Our top choices for Winchester bed & breakfast

Exterior

1. Glen Gordon Manor

Glen Gordon Manor
3.5 star property
Huntly
9.8 out of 10, Exceptional, (98 reviews)
"Staff was efficient, professional, personable, thoughtful. Facilities were lovely, Breakfast was excellent."
United States
Alexander and Judith
$339 nightly
The price is $391
Sep 21 - Sep 22
Total with taxes and fees
Glen Gordon Manor
Front of property

2. Hillbrook Inn

Hillbrook Inn
4.0 star property
Charles Town
8.6 out of 10, Excellent, (691 reviews)
"It was beautiful location. The staff was amazing and the food was excellent highly recommend."
United States
Cecile
$168 nightly
The price is $185
Oct 14 - Oct 15
Total with taxes and fees
Hillbrook Inn
Reception

3. Loudoun Valley Manor

Loudoun Valley Manor
3.0 star property
Waterford
9.6 out of 10, Exceptional, (331 reviews)
"Great location and service. A perfect weekend getaway from DC or Richmond."
United States
Mindi
$150 nightly
The price is $171
Sep 20 - Sep 21
Total with taxes and fees
Loudoun Valley Manor
Reception

4. Light Horse Inn

Light Horse Inn
2.0 star property
Harpers Ferry
9.4 out of 10, Exceptional, (145 reviews)
"This is a very nice and relaxing inn with very helpful staff"
United States
David
$165 nightly
The price is $177
Oct 6 - Oct 7
Total with taxes and fees
Light Horse Inn
Hallway

5. Inn at Evergreen

Inn at Evergreen
3.5 star property
Haymarket
9.4 out of 10, Exceptional, (140 reviews)
"A very beautiful experience. The staff was amazing. The country club access was such a treat. The room was breathtaking. We can’t wait to go back:"
United States
Adriane
$259 nightly
The price is $295
Sep 20 - Sep 21
Total with taxes and fees
Inn at Evergreen
Exterior

6. Bird Nest Suite In Town!- Inside the Grand Castalian Inn B&B

Bird Nest Suite In Town!- Inside the Grand Castalian Inn B&B
Berkeley Springs
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful house. Renovations are not quite complete yet, and the electronic locks needed extra communication with the owner to use, but still a great stay. Perfect location and this place will be gorgeous after renovations are complete."
United States
Daniel F.
$279 nightly
The price is $310
Sep 20 - Sep 21
Total with taxes and fees
Bird Nest Suite In Town!- Inside the Grand Castalian Inn B&B
Outdoor dining

7. The Van Gogh Room in Villa

The Van Gogh Room in Villa
Purcellville
9.0 out of 10, Wonderful, (71 reviews)
"Perfect idyllic retreat -- lovely property, cozy room, AMAZING art and chill vibes. Lovely host, too. Would love to go back :)"
United States
Anonymous traveler
$370 nightly
The price is $422
Sep 20 - Sep 21
Total with taxes and fees
The Van Gogh Room in Villa
Exterior

8. Cozy Lakefront 1 BR 1 Full Bath w/ Private Island Access & Breakfast Included

Cozy Lakefront 1 BR 1 Full Bath w/ Private Island Access & Breakfast Included
Purcellville
10.0 out of 10, Exceptional, (2 reviews)
"We only spent one night here because my wife had training in the town of Purcellville. However, we were treated like family. Kenny, the general manager, was very kind, welcoming and attentive. He personally prepared our breakfast. Noé, the caretaker was wonderful and always available to us. Beyond that, this is one of the most beautiful, scenic properties I have ever experienced. You have to see it for yourself. Highly recommended!"
United States
Andrew
$316 nightly
The price is $360
Sep 24 - Sep 25
Total with taxes and fees
Cozy Lakefront 1 BR 1 Full Bath w/ Private Island Access & Breakfast Included
Garden

9. Hopkins Ordinary Bed Breakfast and Ale Works

Hopkins Ordinary Bed Breakfast and Ale Works
3.0 star property
Sperryville
9.8 out of 10, Exceptional, (38 reviews)
"Staff was wonderful and caring! Breakfast was delicious. The tavern had wonderful beer and we enjoyed meeting Norman the beagle."
United States
Deborah
$308 nightly
The price is $355
Sep 22 - Sep 23
Total with taxes and fees
Hopkins Ordinary Bed Breakfast and Ale Works
Outdoor dining

10. Monet HoneymoonSuite in villa.Elegant Lrg 2rm w/balcony, jacuzzi n phenom.view.

Monet HoneymoonSuite in villa.Elegant Lrg 2rm w/balcony, jacuzzi n phenom.view.
Purcellville
9.8 out of 10, Exceptional, (39 reviews)
"Beautiful location, quiet, and Maud is a wonderful person."
United States
Dennis G.
$483 nightly
The price is $551
Sep 21 - Sep 22
Total with taxes and fees
Monet HoneymoonSuite in villa.Elegant Lrg 2rm w/balcony, jacuzzi n phenom.view.
Porch

11. Gay Street Inn

Gay Street Inn
3.5 star property
Washington
10.0 out of 10, Exceptional, (36 reviews)
"Super cute place! Drew was so helpful and friendly. Loved the breakfast and the whole vibe of the house. Highly recommend,"
United States
Kathryn
$359 nightly
The price is $387
Sep 23 - Sep 24
Total with taxes and fees
Gay Street Inn
Front of property

12. The Carriage Inn B&B

The Carriage Inn B&B
3.5 star property
Charles Town
9.6 out of 10, Exceptional, (456 reviews)
"Amazing place with incredible history!"
United States
Andrea
$155 nightly
The price is $176
Oct 5 - Oct 6
Total with taxes and fees
The Carriage Inn B&B
Interior entrance

13. The Inn at Grass Roots Hill

The Inn at Grass Roots Hill
3.0 star property
Purcellville
9.2 out of 10, Wonderful, (10 reviews)
"Beautiful venue, great service, and very close to the local downtown. Would stay again, highly recommend. "
United States
Robert
$648 nightly
The price is $739
Sep 20 - Sep 21
Total with taxes and fees
The Inn at Grass Roots Hill
Exterior

14. Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event

Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event
Lovettsville
10.0 out of 10, Exceptional, (1 review)
"Everyone was so kind, house was beautiful and the food was amazing. Really made us feel like home. Highly recommend."
United States
Lukas D.
$12,974 nightly
The price is $15,365
Sep 20 - Sep 21
Total with taxes and fees
Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event
Exterior

15. Appalachian Suite In Town!- The Grand Castalian Inn B&B

Appalachian Suite In Town!- The Grand Castalian Inn B&B
Berkeley Springs
10.0 out of 10, Exceptional, (2 reviews)
"We loved the spot and will be back!"
United States
Seth W.
$296 nightly
The price is $328
Sep 21 - Sep 22
Total with taxes and fees
Appalachian Suite In Town!- The Grand Castalian Inn B&B
Exterior

16. River Retreat Suite In Town!- Inside The Grand Castalian Inn B&B

River Retreat Suite In Town!- Inside The Grand Castalian Inn B&B
Berkeley Springs
10.0 out of 10, Exceptional, (4 reviews)
"My partner and I have both stayed in some pretty high end hotels and we were so impressed!! By far the best VRBO i’ve stayed in-newly renovated and decorated. You don’t want to pass up this hidden gem convenient to everything in Berkeley Springs!"
United States
Deirdre A.
$292 nightly
The price is $324
Sep 20 - Sep 21
Total with taxes and fees
River Retreat Suite In Town!- Inside The Grand Castalian Inn B&B
Exterior

17. 50's Drive-In Inside the Grand Castalian Inn B&B

50's Drive-In Inside the Grand Castalian Inn B&B
Berkeley Springs
10.0 out of 10, Exceptional, (1 review)
$305 nightly
The price is $339
Sep 20 - Sep 21
Total with taxes and fees
50's Drive-In Inside the Grand Castalian Inn B&B
Exterior

18. Lakefront Gateway 1 BR 1 Full Bath w/ Private Island Access & Breakfast Included

Lakefront Gateway 1 BR 1 Full Bath w/ Private Island Access & Breakfast Included
Purcellville
$355 nightly
The price is $405
Sep 24 - Sep 25
Total with taxes and fees
Lakefront Gateway 1 BR 1 Full Bath w/ Private Island Access & Breakfast Included
Exterior

19. Peaceful Lakefront 1BR 1 Full Bath w/ Private Island Access & Breakfast Included

Peaceful Lakefront 1BR 1 Full Bath w/ Private Island Access & Breakfast Included
Purcellville
$395 nightly
The price is $450
Sep 24 - Sep 25
Total with taxes and fees
Peaceful Lakefront 1BR 1 Full Bath w/ Private Island Access & Breakfast Included
Exterior

20. 5BR Lakefront Estate w/Private Island Access / Entire House + Breakfast Included

5BR Lakefront Estate w/Private Island Access / Entire House + Breakfast Included
Purcellville
$2,507 nightly
The price is $2,858
Sep 24 - Sep 25
Total with taxes and fees
5BR Lakefront Estate w/Private Island Access / Entire House + Breakfast Included
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winchester Hotel Reviews

Quality Inn Winchester

Quality Inn Winchester

10/10 Excellent
"Clean room, Denny's attached to hotel is very convenient. Continental breakfast included biscuits and gravy, specialty teas and juices. Though the hotel is fairly close to the road, the room was quiet. Will book again if we are in the area"
Mary 1-night trip
Posted 2 hours ago
Quality Inn Winchester

Find out more about Winchester

Winchester B&B information

Number of reviews
1,118
Accommodation
47 B&B
Lowest Price
$171
Highest Price
$739

Frequently asked questions

What is the nightly rate for a Bed and Breakfast in Winchester?
Prices for B&Bs in Winchester often vary, but you can find a great deal from $171 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Winchester B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a Bed and Breakfast in Winchester?
The best time to book a B&B in Winchester is during the vibrant fall months of September and October. This period attracts travelers looking to experience the stunning autumn foliage and partake in various local events, all while enjoying the comfortable temperatures ranging from the mid-50s to low 70s Fahrenheit. The scenery is particularly enchanting as the leaves change, creating a picturesque backdrop for outdoor activities such as hiking the nearby trails or exploring the charming downtown area.

September often sees a delightful mix of warm days and cool evenings, making it ideal for leisurely strolls through local parks or visiting historical sites. The community also hosts several festivals celebrating the harvest, offering visitors a taste of local culture and cuisine.

For those seeking a more budget-friendly experience, consider planning your trip in November. This quieter month provides a unique opportunity to explore Winchester's attractions without the crowds, and you can enjoy the area's natural beauty as the landscape transitions into winter.
What is the difference between a Winchester Bed & Breakfast and a hotel?
Every Winchester B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Winchester B&Bs.

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